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$999,000
3 Beds ⋅ 2 Baths ⋅ 1027975 MLS
ATTEENTION WORK-AT -HOME PROFESSIONALS AND THOSE SEEKING MOTHER DAUGHTER SET UP! Discover a true Pleasantville unicorn — a charming 1930’s single family home with legal commercial ground floor space offering rare flexibility, unbeatable walkability, and the kind of village convenience buyers dream about. Perfectly situated just 0.2 miles to the Pleasantville Metro-North Station, 0.4 miles to Bedford Road School, and 0.3 miles to both the Middle and High Schools, this home delivers effortless access to every part of town. Shops, dining, parks, the Farmers Market, and the Jacob Burns Film Center are all moments away, with easy ON/OFF access to the Saw Mill River Parkway for seamless commuting. County Tax classification code is R-02, the ground-floor unit is a standout feature — ideal as a professional home office (light business permitted) or as a 750 sq ft above ground living space. Previously used as a real estate office, it now functions as a comfortable residential space with endless potential with private entrance and second egress. . The main 3-bedroom apartment offers classic warmth and modern convenience, featuring a chef’s stove, EI kitchen w. SGD onto patio, formal dining room, sun room and living room. The second floor offers f primary bedroom, and two additional secondary bedrooms . The home has been fairly well maintained and is ready for you to personalize and make your own. This home offers off-street parking for at least three vehicles. With flexible zoning, walk-to-everything convenience, and timeless 1930’s character, 4 Depew Street is a one-of-a-kind Pleasantville opportunity. Zoning allows for 6 foot signage that is visible from Saw Mill River Parkway. .

4 Depew Street, Pleasantville
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 1013140 MLS
Pride of ownership is evident throughout this impeccably maintained home and beautifully landscaped property. Set on over an acre in highly sought-after Pleasantville, this classic four-bedroom center hall Colonial, with a stately brick façade, offers timeless elegance and gracious living. Step inside to discover generously proportioned rooms filled with traditional charm. The expansive living room stretches the full width of the home and is bathed in natural light from eastern, southern, and western exposures. A wood-burning fireplace serves as a warm focal point, while a wall of windows showcases picturesque views of mature trees, a tranquil pond, and abundant wildlife. The formal dining room is perfectly suited for both holiday entertaining and intimate gatherings. The spacious eat-in kitchen, complete with two pantries, provides direct access to an expansive deck—ideal for outdoor dining—and the attached two-car garage. A convenient powder room completes the main level. Upstairs, you’ll find a gracious primary suite, three additional bedrooms, and a beautifully renovated full hall bath. The lower level offers remarkable versatility, featuring a welcoming family room with a fireplace, as well as a workshop, laundry area, ample storage space and more. Wood floors, crown molding, central air-conditioning and an oversized two car garage are just some of the special features you will enjoy. The grounds are truly extraordinary, highlighted by exquisite stonework, garden beds, and meticulously maintained landscaping. The backyard invites out door fun, recreation and relaxation, while serene water views create a breathtaking natural backdrop. This stately home boarders scenic Opperman's Pond, where all-season activities from fishing and birdwatching to ice skating - can be enjoyed. This exceptional property is more than a home—it will be your sanctuary offering comfort, beauty, and memories.

1 Woodland Drive, Pleasantville
$3,350,000
5 Beds ⋅ 6 Baths ⋅ 1023249 MLS
Welcome to one of Pleasantville's most exceptional luxury estates—a builder's own masterpiece where timeless elegance, impeccable craftsmanship, and sophisticated design come together in perfect harmony. Ideally located within the highly acclaimed Byram Hills School District, just moments from the charming hamlet of Armonk, this extraordinary residence offers over 7,000 square feet of thoughtfully curated living space designed for the most discerning buyer. From the moment you step inside, you're greeted by soaring ceilings, sun-filled interiors, and beautifully appointed living spaces that seamlessly blend everyday comfort with grand-scale entertaining. Every detail has been carefully considered, creating an atmosphere of refined luxury throughout. The home's versatile floor plan features five spacious bedrooms, including a desirable first-floor guest suite with a full bath—perfect for extended family, overnight guests, or a private executive home office. The spectacular primary suite is a private sanctuary unlike any other, offering a spacious bedroom retreat, expansive custom walk-in closets, and luxurious his-and-her spa-inspired bathrooms, providing the ultimate in comfort, privacy, and everyday indulgence. Designed for effortless indoor-outdoor living, the resort-style backyard is an entertainer's dream. Spend summer days relaxing beside the stunning in-ground pool and spa or host unforgettable gatherings beneath the covered patio, complete with built-in heaters, integrated speakers, and a fully equipped outdoor kitchen—allowing you to enjoy every season in style. The expansive walk-out lower level offers endless possibilities, whether you envision a state-of-the-art home theater, fitness center, game room, wine cellar, or additional living quarters. Its exceptional scale provides the flexibility to accommodate every lifestyle. Perfectly positioned in one of the area's most desirable neighborhoods, this remarkable estate is just minutes from Armonk's vibrant downtown, Metro-North, award-winning schools, fine dining, boutique shopping, parks, and convenient access to New York City.

15 Heritage Drive, Pleasantville
$2,100,000
6 Beds ⋅ 5 Baths ⋅ 944741 MLS
Welcome to this extraordinary estate, a gem dating back to the 1900s, situated on over an acre of picturesque land. This sunlit residence boasts 6 spacious bedrooms and 4 1/2 bathrooms, making it the perfect sanctuary for entertaining guests. Step inside to experience the remarkable craftsmanship that defines this home. With oversized rooms designed for both formal gatherings and casual moments, you’ll find ample space to create lasting memories. The property features an amazing garden and a fenced outdoor area ideal for summer gatherings and outdoor enjoyment. Conveniently located near Pleasantville, Armonk, and Chappaqua, you’ll have easy access to shopping, dining & Metro North. Don’t miss your chance to own this one-of-a-kind home.

235 Bear Ridge Road, Pleasantville

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.